Budwig Diet – The Science of a Superfood in the Prevention of Chronic Diseases

A Short Discussion of the Chemistry of Fatty Acids – Linoleic and Alpha-Linolenic Acids

The two fatty acids most vital to human life are linoleic acid (LA) and alpha-linolenic acid (α-linolenic acid, ALA). They are both polyunsaturated fats and they both have 18 carbon compounds in their chains. They are also classified as essential fatty acids (EFAs). They are called “essential” because they are required for good health and biological functions but the body cannot synthesize them – therefore, all sources of EFAs must come from food. There are other fatty acids that are also important, but since they can be biosynthesized, they are not classified essential. There are also “conditionally essential” fatty acids that become essential only under conditions in which the body cannot convert them, e.g. disease conditions or when there is a deficiency of the essential fatty acids. So, “essential” is a classification given to organic compounds that cannot be biosynthesized and must come from the diet. Dr. Budwig considered linoleic acid and linolenic acids (alpha and gamma) vital essential fatty acids.

At this point, I must expand a little bit on chemistry. At some point, it is inevitable. I find this topic to be quite interesting actually. In order to understand Dr. Budwig’s scientific findings and the importance of the essential fatty acids, it helps to know some general ideas about their chemistry.

The Chemistry of Fatty Acids

Structural formula of Lauric Acid, a saturated fatty acid.

Sample structural formula of a fatty acid molecule: one end is the carboxyl group, COOH (right), and the other end, ω or n, is the methyl group, CH3 (left); middle compounds are a series of repeating CH2. All fatty acids have an even number of carbon compounds and follow this pattern, varying in the number of carbon atoms and the bonding between them. Here, 12 carbon atoms and all single bonds indicate that this is lauric acid (dodecanoic acid), a medium-chain saturated fatty acid that is the main constituent of coconut oil, palm kernel oil and laurel oil (50%). Molecular formula: C12H24O2.

Simply speaking, a fatty acid is an organic molecule consisting of a chain or tail of carbon compounds with a total even number of carbon atoms ranging from 4 to 28.{1}Entry for “fatty acids”. IUPAC. Compendium of Chemical Terminology, 2nd ed. (the “Gold Book”). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford, 1997. ...continue The beginning of the chain is always a carboxyl group (COOH) and the end of the chain, the omega (ω) or n end, is always a methyl group (CH3), while the middle compounds are a series of repeating methylene bridges (CH2) – or, in the case of unsaturated bonds, just CH – bonded in a zig-zag shape.

In saturated fatty acids, each carbon compound is connected to another carbon compound by a single bond – i.e. two carbon atoms share two electrons between them. Their other bonds are saturated with hydrogen atoms (and oxygen). All saturated fatty acids have only single bonds and contain the maximum amount of hydrogen.

Fatty acids are unsaturated when, somewhere along the chain, one or more of the carbon-to-carbon bonds is a double bond – i.e. two carbon atoms share four electrons between them. By sharing two bonds with another carbon, each carbon has “lost” a hydrogen atom – therefore, each double bond has two fewer hydrogen atoms and thus, is called unsaturated (with hydrogen).

Structural formula of Oleic Acid, a monounsaturated fatty acid.

Sample structural formula of an unsaturated fatty acid molecule: this chain has 18 carbon atoms and one double bond, making it monounsaturated. The double bond occurs at the 9th carbon counting from the methyl carbon (CH3) – ω-9 or n-9. Middle links are CH2 except at the double bond: since the carbon atom is sharing two bonds with another carbon, each carbon has to give up one hydrogen atom (CH). This is oleic acid, the majority constituent of olive oil (70%). Molecular formula: C18H34O2.

Unsaturated fatty acids are classified based on the number of carbon atoms and how many carbon-to-carbon double bonds they possess and the double bonds’ position within the chain.{2}“Fat”. Wikipedia. The fatty acids of interest to us are those with 18 carbon compounds.

Oleic acid, linoleic acid and alpha-linolenic acid all have 18 carbon compounds. The difference between them is the number of double bonds that they possess – and to Dr. Budwig, this is the key that makes all the difference in the world!

Oleic acid has one double bond; therefore, it is called monounsaturated because it is unsaturated only once. This double bond is located at the 9th carbon counting from the methyl carbon end – the omega-9 position (C18:1, n-9).{3}“Oleic acid”. Wikipedia. Fatty acids with two or more double bonds are polyunsaturated. (Recall: Dr. Budwig in her books calls them “highly unsaturated”. I will use this term also since that was the term in her books.) Linoleic acid has two double bonds, with the first double bond occurring at the 6th carbon from the methyl carbon end – the omega-6 position (C18:2, n-6).{4}“Linoleic acid”. Wikipedia. alpha-Linolenic acid has three double bonds, with the first double bond located at the 3rd carbon from the methyl end – the omega-3 position (C18:3, n-3).{5}“alpha-Linolenic acid”. Wikipedia.

Structural formula of Linoleic Acid, a double unsaturated fatty acid.

This structural formula shows linoleic acid with two double bonds, making it double unsaturated. The first double bond occurs at the 6th carbon counting from the methyl carbon (CH3) – ω-6 or n-6. Molecular formula: C18H32O2.

Carbon-to-carbon double bonds are geometrically rigid and non-rotatable, and cause the chains to bend in a geometric configuration called cis. In the cis double bond, the hydrogen atoms lie on the same side of the carbon atoms relative to a reference plane, causing the bent shape. The more double bonds there are, the more pronounced is the bend in the chain. When the hydrogen atoms lie on opposite sides of the reference plane, the double bond forms a trans configuration.{6}Entry for “cis-trans”. IUPAC. Compendium of Chemical Terminology, 2nd ed. (the “Gold Book”). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford, 1997. ...continue{7}Entry for “cis-trans isomers”. IUPAC. Compendium of Chemical Terminology, 2nd ed. (the “Gold Book”). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford, ...continue In a trans configuration, the chains are more or less straight on both sides of the double bonds, similar to the straight geometry of natural saturated fatty acids with their rotatable single bonds; e.g. lauric acid. With rare exceptions, most naturally occurring double bonds have cis configurations; the trans configuration forms from artificial treatment processes such as hydrogenation. Unsaturated oils that have undergone hydrogenation still possess a leftover number of double bonds, but the treatment alters the positions of the hydrogen atoms, thus changing their cis form into the trans form; these partially hydrogenated fats are called trans fats.{8}“Fatty acid”. Wikipedia.

Structural formula of alpha-Linolenic Acid, a triple unsaturated fatty acid.

alpha-Linolenic acid has three double bonds, making it triple unsaturated. The first double bond occurs at the 3rd carbon from the methyl carbon (CH3) – ω-3 or n-3. Molecular formula: C18H30O2. Note: gamma-Linolenic acid, GLA (not shown), an isomer of alpha-linolenic acid, also has three double bonds, occurring at the 6th, 9th and 12th carbons – ω-6.

Linoleic and alpha-linolenic acids are the raw materials for the body to convert to longer-chain fatty acids and conjugated fatty acids. For example, alpha-linolenic acid is further biosynthesized into stearidonic acid (SDA), a fatty acid with 18 carbons and four double bonds starting at omega-3 (C18:4, n-3){9}“Stearidonic acid”. Wikipedia.. Linoleic and alpha-linolenic acids themselves cannot be biosynthesized. Scientifically, these acids are known as electron-rich essential highly unsaturated fatty acids. These are the prized acids, the vital and essential fatty acids!

A small note about other important fatty acids

There are three other fatty acids that need to be briefly mentioned here.

Three-dimensional illustration of oleic acid molecule.

The oleic acid molecule is naturally bent at the double bond due to the inflexibility of the bonding. This type of configuration is called cis and is characteristic of natural unsaturated fatty acids. Treatment processes such as partial hydrogenation change the geometry of the double bond to a straight configuration, called trans. Unsaturated fats that contain straight double bonds in the fatty acid chains are called trans fats. Because fatty acids make up the physical structure of the cell membranes, which control all functions into and out of the cell, the trans fatty acids with their unnatural geometry have detrimental effects to the biological processes. (artwork: courtesy, Ben Mills, UK, released to the public domain, Wikimedia Commons)

Three-dimensional illustration of elaidic acid molecule.

Compare the cis oleic acid to the trans elaidic acid molecule. Note the unnaturally straight configuration of the double bond at the omega-9 carbon. With 18 carbon compounds and one trans double bond (C18:1, n-9), elaidic acid is a geometric isomer of oleic acid. They have the same chemical structure and molecular formula, but different geometric configurations (elaidic acid is also called “trans-oleic acid”). Elaidic acid is the result of artificial processing such as hydrogenation. (artwork: courtesy, Ben Mills, UK, released to the public domain, Wikimedia Commons)

Ball and stick model of stearic acid molecule.

Compare the trans elaidic acid to the saturated stearic acid molecule (octadecanoic acid). Stearic acid is naturally straight due to all single bonds. Stearic acid is neither cis nor trans because it has no carbon-to-carbon double bonds. With 18 carbon compounds and no double bonds (C18:0), stearic acid is the saturated counterpart of oleic acid. (artwork: courtesy, Ben Mills and Jynto, released to the public domain, Wikimedia Commons)

It is worth noting that gamma-linolenic acid (γ-linolenic acid, GLA) has 18 carbons and three double bonds just like alpha-linolenic acid, the only difference being that the first double bond of GLA occurs at the 6th carbon – the omega-6 position (C18:3, n-6). In fact, gamma-linolenic acid is an isomer of alpha-linolenic acid: they share the same molecular formula but different chemical structures. Note: In the three books that have been translated into English, Dr. Budwig does not differentiate between these two fatty acids. She refers to them collectively as linolenic acids: “the triple unsaturated fatty acids…were called linolenic acid, and which no one had isolated before me, had 18 links and that they did not always carry their double bonds at the same point.”{10}Budwig, J. Cancer – The Problem and the Solution, p. 20.

“…at the same point” – This was a source of confusion for me for a long time, as I could not understand when or how the location of the three double bonds in alpha-linolenic acid would change (since it wouldn’t be classified omega-3 if the position changed) – until I finally realized that she was referring to another fatty acid, gamma-linolenic acid! If my interpretation is correct, then, for Dr. Budwig, GLA is also a vital essential fatty acid due to its 18 carbons and three double bonds, and rather than GLA being a separate fatty acid, she considered it as essential linolenic acid with the double bonds in a different position. (Again, my apologies if I have interpreted this wrong.)

For the purposes of this article, I have differentiated alpha-linolenic acid from “linolenic acids” and gamma-linolenic acid for these reasons: 1) GLA is not found in significant amounts in flaxseed oil; 2) GLA can be bio-produced from linoleic acid and so is not “essential”; and 3) in order to be consistent with current classifications to avoid confusion. Nevertheless, GLA remains an important vital fatty acid and when the body cannot manufacture GLA (such as when there is a deficiency of linoleic acid), it becomes essential and must be supplemented from diet. Plant sources high in GLA include borage oil, evening primrose oil and the fresh-water algae, spirulina. There are even fewer foods with significant amounts of GLA. This is all the more reason why adequate levels of the linoleic and alpha-linolenic acids must be a vital part of the diet.

The other two fatty acids I would like to mention are the very long chain fatty acids: eicosapentaenoic acid (EPA) with 20 carbons and five cis double bonds (C20:5, n-3);{11}“Eicosapentaenoic acid”. Wikipedia. and docosahexaenoic acid (DHA) with 22 carbons and six cis double bonds (C22:6, n-3).{12}“Docosahexaenoic acid”. Wikipedia. Both are omega-3 fatty acids. These fatty acids’ high number of double bonds gives them great electron energy. EPA and DHA are found in oily fish and algae. Fish or liver oils are ideal for the body due to the numerous unsaturated bonds allowing them to associate with protein and providing materials for new growth. Both EPA and DHA are bio-converted from alpha-linolenic acid, but the efficiency is a few percent. As with GLA, if the body cannot produce them (due to disease or other conditions), then they must be supplemented from the diet.

Three-dimensional illustration of alpha-linolenic acid molecule.

The cis alpha-linolenic acid molecule has a candy cane shape due to three bends in the three double bonds at the 3rd, 6th and 9th carbons. Due to their shape, the molecules do not pack tightly together. (artwork: courtesy, Ben Mills, UK, released to the public domain, Wikimedia Commons)

Although these two fatty acids are highly ideal, for practical purposes, Dr. Budwig did not recommend taking fish oils on a regular basis due to the industrial processing methods used to extract them from fish. Many commercial sources of fish oils are oxygen stabilized to delay rancidification, thus rendering them inert and unable to perform oxidation at the cellular level. Additionally, once fatty acids have been converted into long-chain fatty acids, EPA and DHA, they cannot be bio-converted back into the shorter chain linoleic and linolenic acids, which are needed for other biological processes.

Fish sources of these fatty acids are becoming increasingly problematic today due to: the high levels of mercury, industrial contaminants and other toxins as the oceans are becoming more polluted; the prevalence of farmed fish which are fed processed food which do not produce the same nutrients and fatty acids as those of wild fish; and, the heat from cooking fish will damage the oils to some extent. It is best to extract the oil raw and to remove toxic contaminants in the process; for these reasons, fish and cod liver oils are popular as dietary supplements, but it is crucial to find a quality brand. Additionally, unlike humans, fish do not produce EPA and DHA naturally, but get them from the algae that they eat.{13}Bishop-Weston, Y. “Plant Based Sources of Vegan & Vegetarian Docosahexaenoic Acid DHA and Eicosapentaenoic Acid EPA & Essential Fats”. Foods for Life website. Therefore, consuming algae or krill oil high in these fatty acids will give you a good source of ready-made EPA and DHA, and bypasses the problems of eating fish.

Due to the numerous other fatty acids that are bio-converted from the essential fatty acids, linoleic and alpha-linolenic acids should be properly supplemented. It becomes clear how vital linoleic acid and alpha-linolenic acid are for all the biological functions.

Relationship of Fatty Acids to Fats – Triglycerides

What is the difference between fats, oils and fatty acids?

Diagram of triglyceride molecule consisting of palmitic acid, oleic acid and alpha-linolenic acid.

Diagram of a sample triglyceride molecule consisting of three arms of fatty acids (right) bonded to glycerol (left). (Carbon atoms are not shown; each corner in the zig-zag represents a carbon compound.) From top to bottom: 1) palmitic acid (16 carbon compounds, all single bonds, saturated); 2) oleic acid (18 carbon compounds, one double bond, monounsaturated); 3) alpha-linolenic acid (18 carbon compounds, three double bonds, polyunsaturated). (artwork: courtesy, Wolfgang Schaefer, Seoul, Korea, released to the public domain, Wikimedia Commons)

Three dimensional illustration of a triglyceride molecule.

Three dimensional illustration of a triglyceride molecule showing three cis fatty acid chains bonded to a glycerol backbone. (artwork: courtesy, Ben Mills, UK, released to the public domain, Wikimedia Commons)

A triglyceride of sunflower oil derived from two chains of linoleic acid and one chain of oleic acid.

Diagram of a triglyceride of sunflower oil (carbon compounds not shown) derived from two chains of linoleic acid (two double bonds) and one chain of oleic acid (one double bond), making this a ratio of 2:1. (artwork: courtesy, Smokefoot, Wikimedia Commons. Used under a Creative Commons Attribution-Share Alike License.)

Fats are a subgroup of the larger group of lipids. Lipid is a group of natural organic molecules that are soluble in non-polar solvents and include fats and oils (glycerides), waxes, sterols (e.g. cholesterol), fat-soluble vitamins, phospholipids and others.{14}Entry for “lipids”. IUPAC. Compendium of Chemical Terminology, 2nd ed. (the “Gold Book”). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford, 1997. On-line ...continue Fatty acids are the single molecules that form fats, phospholipids and some natural waxes. In nature, fatty acids do not occur naturally as free flowing molecules. In fats and oils, they are found in groups of three: an ester of three fatty acids bonded together by a backbone, glycerol (an alcohol) – called a triglyceride molecule (“triester of glycerol”).{15}“Fat”. Wikipedia. It resembles a capital E. When three fatty acids react with glycerol, they form fats.

Fats and oils are essentially made up of triglycerides of fatty acids – the triglyceride molecule is the greasy material itself. “Oil” is usually used to refer to fats that are liquids at room temperature.{16}“Fat”. Wikipedia. Thus, storage fats in human and animal tissues are called “fats”, while coconut oil is called “oil” even though it is a solid below 76° F (25° C) – i.e. it is liquid in its natural tropical environment. The three tails of the triglyceride can be the same or different fatty acid chains. Triglycerides are the main constituents of fats and oils, whose characteristics are determined by the types of fatty acids bound in the triglyceride molecules.{17}“Triglyceride”. Wikipedia.

Olive oil is composed predominantly of triglycerides of oleic acid, which is named for the oil. With between 55 to 83% oleic acid (70% average), 3.5 to 21% linoleic acid, and 7.5 to 20% palmitic acid (16 carbons, saturated, C16:0),{18}“Olive Oil: Chemical Characteristics”. Olive Oil Source. N.p., n.d. Web. olive oil is mainly a monounsaturated omega-9 oil. Oleic acid, being more stable than the omega-6 and omega-3 fatty acids and found in abundance in food, does not need to be supplemented. With most of its constituents being oleic acid with one double bond, olive oil is not a bad or harmful oil, but neither is it the most vital, according to Dr. Budwig. However, as an oil, olive oil has cultural and religious importance to many societies, especially those of the Mediterranean and the Near East.

Sunflower oil is a mixture of mostly oleic acid (30%) and linoleic acid (59%), the rest being small percentages of other fatty acids.{19}“Sunflower oil”. Wikipedia. In a typical oil, the ratio of omega-9 to omega-6 is 1:2. With a combined 90% of its fatty acids having single double bonds and double double bonds, and twice as much linoleic acid as oleic acid, sunflower oil is a good food for the vital functions and biological processes.

Bottle of cold-pressed sunflower oil.

Sunflower oil has a lighter yellow color than flaxseed oil.

Walnut oil is extracted from English walnuts, similar in composition to sunflower oil. Dr. Budwig did not specifically mention walnut oil (although it is included collectively with seed oils), so I would like to mention it here because, based on its constituents, it may be even better than sunflower oil: 22.2% oleic acid, 52.9% linoleic acid and 10.4% alpha-linolenic acid.{20}“Walnut oil”. Wikipedia. These are very good fatty acid constituents, making walnut oil a good substitute for sunflower oil (i.e. based on constituents alone, everything else being equal).

Flaxseed oil (also called linseed oil) is in general a mixture of 17% oleic acid, 15% linoleic acid, 57% alpha-linolenic acid, 7% palmitic acid, 3-4% stearic acid (18 carbons, saturated, C18:0) and small quantities of other fatty acids.{21}“Linseed oil”. Wikipedia. Flaxseed oil has an unusually large amount of alpha-linolenic acid, one of the few foods that do. Other oils high in alpha-linolenic acid include kiwifruit seeds, perilla seeds and chia seeds.

With its high number of single, double and triple double bonds, flaxseed oil is highly reactive with oxygen and light, causing it to go rancid quickly. Since omega-3 oils are more fragile and less stable, they are harder to find undamaged; omega-6 oils are more stable and found in more abundance in foods. Too much omega-6 fatty acids (even linoleic acid), however, with too little omega-3 can throw the vital functions out of balance because the two types compete for absorption. Therefore, consuming flax oil will help to counterbalance the ratio of omega-3 to omega-6 fatty acids in the diet, a ratio that is of importance to biological and metabolic functions.

The combination of linoleic–linolenic fatty acids gives flaxseed oil the highest collection of electron energy. With its ratio of 1 to 3, linoleic acid to alpha-linolenic acid, these fatty acids are well combined in flax oil. With these constituents, flaxseed oil is the crème de la crème. It is the best oil that Dr. Budwig knew of that has this combination of double and triple double bonds. With its double and triple unsaturation in a large quantity, flaxseed oil is a highly unsaturated fat – the ideal oil for blending with high sulfur protein for oxygen absorption – that is, the Budwig diet.

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